The 'How to Wear a Men's Shirt' meme originates from online fashion tutorials and life hacks that claim a man's button-down can be effortlessly transformed into a stylish dress or skirt. The meme version subverts this 'Pinterest-perfect' expectation by showing the increasingly absurd or unflattering results of trying to follow these instructions. It often highlights the gap between expectation and reality, where the final image depicts the person looking like a potato sack, a ghost, or a bizarre creature. It is a staple of relatable internet humor, particularly within communities that poke fun at unrealistic fashion trends and DIY culture.